3160-47-2

Basic information

• Product Name: Z-ASP(OME)-OH
• Synonyms: CBZ-L-ASPARTIC ACID 4-METHYL ESTER;CBZ-ASP(OME)-OH;N-ALPHA-CARBOBENZOXY-L-ASPARATIC ACID BETA-METHYL ESTER;N-BENZYLOXYCARBONYL-L-ASPARTIC ACID 4-METHYL ESTER;N-CBZ-L-ASPARTIC ACID BETA-METHYL ESTER;(S)-2-BENZYLOXYCARBONYLAMINO-SUCCINIC ACID 4-METHYL ESTER;(S)-2-N-CBZ-AMINO-SUCCINIC ACID 4-METHYL ESTER;Z-ASP(OME)-OH
• CAS NO: 3160-47-2
• Molecular Formula: C₁₃H₁₅NO₆
• Molecular Weight: 281.26
• EINECS: 1312995-182-4
• Product Categories: Z-Amino Acids and Derivatives;Z-Amino acid series
• Mol File: 3160-47-2.mol

Chemical Properties

• Melting Point: 98 °C
• Boiling Point: 503.6 °C at 760 mmHg
• Flash Point: 258.3 °C
• Appearance: White/Powder
• Density: 1.304 g/cm³
• Vapor Pressure: 5.82E-11mmHg at 25°C
• Refractive Index: 1.539
• Storage Temp.: −20°C
• PKA: 3.63±0.23(Predicted)
• BRN: 6279422
• CAS DataBase Reference: Z-ASP(OME)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-ASP(OME)-OH(3160-47-2)
• EPA Substance Registry System: Z-ASP(OME)-OH(3160-47-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 3160-47-2(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C13H15NO6/c1-19-11(15)7-10(12(16)17)14-13(18)20-8-9-5-3-2-4-6-9/h2-6,10H,7-8H2,1H3,(H,14,18)(H,16,17)/t10-/m0/s1

Upstream product

• 2177-62-0 β-methyl L-aspartate 
• 501-53-1 benzyl chloroformate 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 
• 16856-13-6 (+)-β-methyl-L-aspartate hydrochloride 
• 1152-61-0 N-Cbz-L-Asp 
• 35909-93-4 dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate 
• 67-56-1 methanol 
• 4515-23-5 N-benzyloxycarbonyl-L-aspartic acid anhydride 
• 79-22-1 methyl chloroformate 
• 57933-83-2 Isopropenyl chloroformate 

Downstream Products

• 3330-39-0 N-(Benzyloxycarbonyl)-L-asparaginsaeure-α-(4-nitro-phenyl)-β-methylester 
• 39993-92-5 (S)-2-Benzyloxycarbonylamino-succinic acid 4-methyl ester 1-pentafluorophenyl ester 
• 54430-88-5 (S)-3-Benzyloxycarbonylamino-N-(2,4,6-trichloro-phenoxycarbonylmethyl)-succinamic acid methyl ester 
• 229487-00-7 3-benzyloxycarbonylamino-N-(2-hydroxy-benzyl)-N-methyl-succinamic acid methyl ester 
• 229487-01-8 3-benzyloxycarbonylamino-N-(2,5-dihydroxy-benzyl)-N-methyl-succinamic acid methyl ester 
• 229487-02-9 3-benzyloxycarbonylamino-N-(2,5-dimethoxy-benzyl)-N-methyl-succinamic acid methyl ester 
• 340732-86-7 3-benzyloxycarbonylamino-4-(4-tert-butoxycarbonylmethyl-2-methoxycarbonylmethyl-3-oxo-piperazin-1-yl)-4-oxo-butyric acid methyl ester 
• 129749-01-5 3(S)-Carboxymethyl-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one 
• 129749-00-4 β-Carboxymethyl-N-(2'-benzoylphenyl)aspartamide hydrobromide 
• 1415743-60-0 Z-Asp-Val-Tyr-OH 
• 1621105-58-5 methyl (3S)-(3-amino-4-(N-benzyl-4-(benzylcarbamoyl)piperidin-4-yl)(sec-butyl)amino)-4-oxobutanoate 
• 1621105-59-6 methyl (3S)-3-amino-4-((4-(benzylcarbamoyl)piperidin-4-yl)(sec-butyl)amino)-4-oxobutanoate 
• 1621105-40-5 methyl (3S)-4-((N-benzyl-4-(benzylcarbamoyl)piperidin-4-yl)(sec-butyl)amino)-3-(((benzyloxy)carbonyl)amino)-4-oxobutanoate 
• 1621105-50-7 methyl (S)-4-((N-benzyl-4-(benzylcarbamoyl)piperidin-4-yl)(cyclopropyl)amino)-3-(((benzyloxy)carbonyl)amino)-4-oxobutanoate 

Relevant articles and documents

SuFExable Isocyanides for Ugi Reaction: Synthesis of Sulfonyl Fluoro Peptides

Herein, the sulfonyl fluoro isocyanides were first developed as a new type of SuFExable synthon, and they are used as building blocks in the Ugi reaction (U-4CR). The Ugi reaction was established and the substrate scope was investigated, and various sulfonyl fluoro α-amino amides and peptides could be reached in a one-step synthesis. Therefore, this protocol opens a new vision for SuFExable building blocks and click chemistry, and it also provides a distinct approach to sulfonyl fluoro peptides.

Syntheses of Enantiopure 1,2-Ethylenediamines with Tethered Secondary Amines of the Formula H 2NCH 2CH[(CH 2) nNHMe]NH 2(n = 1-4) from α-Amino Acids: New Agents for Asymmetric Catalysis

Tris(hydrochloride) adducts of the title compounds-are prepared from the inexpensive α-amino acids H 2 N(C=O)CH 2 CH(NH 2)CO 2 H, HO(C=O)(CH 2) n ′ CH(NH 2)CO 2 H (n ′ = 1, 2), and H2 N(CH 2) 4 CH(NH 2)CO 2 H, respectively (steps/overall yield = 5/32, 7/30, 7/33, 5/38). The NH 2 group that is remote from the secondary amine is installed via BH 3 reduction of an amide [-(C=O)NR 2[ derived?-from an α-amino carboxylic acid. The MeNHCH 2 units are introduced by BH 3 reductions of alkyl carbamate [RO(C=O)NHCH 2-; R = Et, t-Bu] or amide [MeHN(C=O)-] moieties.

Synthesis of desmosine-containing cyclic peptide for the possible elucidation of elastin crosslinking structure

Elastin is a vital extracellular matrix protein, which is known for providing elasticity in numerous tissues. It is formed by the self-assembly and subsequent crosslinking of elastin precursor, tropoelastin. Two tetrafunctional, pyridinium-based amino acids desmosine and isodesmosine are exclusively found in elastin and play an important role as crosslinkers. Structural elucidation of elastin has eluded scientists to date, owing to the highly cross-linked structure and insoluble nature. Therefore, in this study, we aimed to synthesize a desmosine-containing cyclic peptide as a partial elastin mimic, in order to eventually facilitate the elucidation of the crosslinking pattern of elastin by mass spectrometric analysis.

FUNCTIONALIZED LINEAR LIGANDS AND COMPLEXES THEREOF

The invention relates to chemical compounds and complexes that can be used in therapeutic and diagnostic applications.

A PREPARATION METHOD OF SITAGLIPTIN

The present invention relates to a preparation method of sitagliptin, and more particularly, to a method of preparing sitagliptin using L-aspartic acid having a (R)-beta amino acid structure by mild amide formation, by the use of industrially applicable halo isopropylmagnesium, and by removal of amine protecting group using Pd/C and H2 and carbonyl reduction using reducing agent.

Synthesis of (-)-dihydropinidine, (2S,6R)-isosolenopsin and (+)-monomorine via a chiral synthon from l-aspartic acid

The use of a β-amino aldehyde derived from l-aspartic acid as a chiral synthon to construct 2,6-disubstituted piperidines is described. The synthesis of (-)-dihydropinidine·HCl, (2S,6R)-isosolenopsin·HCl and (+)-monomorine has been achieved from this chiral synthon using a Wittig reaction followed by hydrogenation (reductive cyclization) as the key steps.

AmIno Acid Homologation by the Blaise Reaction: A new entry into nitrogen heterocycles

(Chemical Equation Presented) A general strategy for the amino acid homologation via Blaise reaction and subsequent reduction is presented. This strategy involves the preparation of protected α-amino nitriles from the corresponding amino acids, followed by the zinc-mediated condensation of tert-butyl bromoacetate, to give the imidazolidones after iminozincate cyclization. Reduction gave the saturated imidazolidinones with cis or trans stereochemistry, depending on the reduction conditions. This strategy was applied to nonfunctionalized amino acids and to functionalized amino acids such as serine and aspartic acid. Additionally, acidic hydrolysis of cis or trans imidazolidinones to the corresponding chiral 4-aminopyrrolidones is described.

Manipulating L-aspartic and L-glutamic acids - Diastereoselective synthesis of enantiopure β-amino-γ-hydroxy acids and γ-amino-δ-hydroxy acids

Enantiopure (3S,4R)- and (3S,4S)-3-amino-4-hydroxyhexanoic acids and (4S,5R)- and (4S,5S)-4-amino-5-hydroxyheptanoic acid derivatives have been prepared by stereodivergent synthesis from L-aspartic and L-glutamic acids, respectively. The stereochemistry at the carbon atom attached to the amino group was determined from the starting material but the configuration at C-4 or C-5 is controlled by diastereoselective alkylation with diethylzinc or ethylmagnesium bromide. The protection of the carboxylic group as OBO orthoester improved the yields in the final products. Wiley-VCH Verlag GmbH & Co, KGaA, 69451 Weinheim, Germany, 2003.

Utility of tetrathiomolybdate and tetraselenotungstate: Efficient synthesis of cystine, selenocystine, and their higher homologues

Efficient synthesis of cystine, selenocystine, and their higher homologues like homo and bishomo amino acid derivatives from natural amino acid derivatives using tetrathiomolybdate and tetraselenotungstate reagents under mild and neutral conditions is reported. The generality of the reaction has been studied by capping various groups to amino and carboxyl components of canonical amino acids.

Synthesis and in vitro enzyme activity of aza, oxa and thia derivatives of bacterial cell wall biosynthesis intermediates

Mechanism based inhibitors of diaminopimelate aminotransferase (DAP-AT) were designed using knowledge of its substrate specificity and mechanism. Synthesis of thiolester and amide substrate analogues was achieved prior to in vitro inhibition studies, but ester analogues proved too unstable to isolate. Thia substrate analogues showed no inhibitory properties, but the aza substrate analogue 12a showed reversible inhibition vs. DAP-AT and time dependent inhibition in the absence of the natural substrate 4. Substrate analogue 12a is thefirst example of an amide inhibitor of PLP dependent enzymes. Antibiotic properties of 12a were also briefly assessed.